Sericosides and method of use

ABSTRACT

Pharmaceutically active compounds of the formula ##STR1## wherein R 1 , R 2 , R 3  and R 4 , which may be the same or different, each represents a hydrogen atom or a substituted or unsubstituted aliphatic or aromatic mono- or poly-carboxylic acid acyl radical and R 5  represents a glycosyl group, are provided together with processes for their production and pharmaceutical compositions containing them. These compounds possess valuable cicatrizing and anti-inflammatory properties.

This is a division, of application Ser. No. 541,588, filed Jan. 16,1975, now abandoned.

This invention relates to novel pharmaceutically active compounds, toprocesses for their production, to pharmaceutical compositionscontaining the compounds and to plant extracts from which the compoundsmay be prepared.

Plants of the genus Terminalia (of the family Combretaceae) aredistributed over regions of Africa, Asia, Australia and tropicalAmerica. We have now discovered that extracts possessing valuablepharmaceutical properties may be obtained from plants of one particularspecies of this genus, namely Terminalia sericea.

These extracts have a high content of terpenic compounds and, inaddition to the known compounds arjunic acid and arjunetine, they havebeen found to contain two hitherto unknown compounds which we have namedsericic acid and sericoside. These compounds are respectively2α,3β,19α,24-tetrahydroxy-olean-12-en-28-oic acid and itsD-glucopyranoside ester, and may be represented by the formula (I)##STR2## wherein in the case of sericic acid, R= hydrogen and in thecase of sericoside, R= glucose.

Sericic acid and sericoside have been found to possess valuablecicatrizing and anti-inflammatory properties which render themparticularly useful in treating dermatological disorders, for example bybeing incorporated into cosmetics and in treating stomach ulcers.Sericic acid and sericoside may also be converted into derivatives whichhave similar valuable pharmacological properties.

Thus in accordance with one aspect of the present invention, there areprovided compounds of the general formula (II) ##STR3## wherein --OR₁,--OR₂, --OR₃ and --OR₄ each represents a free or esterified hydroxylgroup and --R₅ represents a glycosyl group, preferably D-glucopyranosyland pharmaceutically acceptable salts of such compounds which arecapable of salt formation.

R₁, R₂, R₃ and R₄, which may be the same or different, may, for example,be substituted or unsubstituted aliphatic or aromatic mono- orpoly-carboxylic acid acyl radicals, particularly such radicalscontaining up to twelve and preferably up to seven carbon atoms.

The aliphatic mono- or poly-carboxylic acid acyl radicals (bothsubstituted and unsubstituted) may be straight or branched, chained orcyclic and furthermore may be saturated or unsaturated. Examples ofsaturated, unsubstituted aliphatic mono-carboxylic acid acyl radicalsinclude acetyl, propionyl, butyryl, isobutyryl, valeryl, hexanoyl andheptanoyl. Particularly preferred are such radicals containing up tofour carbon atoms.

Examples of poly-carboxylic acid acyl radicals include hemi-maleyl,hemi-fumaryl and hemi-succinyl.

Examples of aromatic carboxylic acid acyl radicals include benzoyl andphenylacetyl.

Where such radicals are substituted, the or each substituent may, forexample, be selected from halogen (i.e. fluorine, chlorine, bromine oriodine), nitro, hydroxy, ether, keto and amino groups. The aromaticmono- or polycarboxylic acid acyl radicals may additionally oralternatively be substituted by one or more aliphatic radicals(optionally substituted, for example by one or more of the substituentsreferred to above) and preferably containing up to six carbon atoms asin methyl, ethyl, propyl, isopropyl, butyl, isobutyl, valeryl and hexyl.

Particularly preferred acyl radicals for R₁, R₂, R₃ and R₄ are acetyl,benzoyl and hemi-succinyl.

Where any one of R₁, R₂, R₃ and R₄ represents an acyl radical derivedfrom a polycarboxylic acid, the remaining carboxyl (--COO--) group orgroups may be in the form of the free acid (--COOH) or in the form of aderivative, for example an acid addition salt with a pharmaceuticallyacceptable cation, or an ester with, for example, an aliphatic alcoholcontaining up to seven carbon atoms, such as, for example, methanol,ethanol, propanol, isopropanol, n-butanol, pentanol, hexanol andheptanol.

Compounds of general formulae (II) containing carboxyl groups (forexample where R₁, R₂, R₃ or R₄ contains a free carboxyl group) may beconverted to pharmaceutically acceptable acid addition salts, forexample with metals yielding pharmaceutically acceptable cations, suchas, for example, sodium, potassium, calcium, magnesium, aluminum oriron. Also, compounds containing substituted or unsubstituted aminogroups may be converted to pharmaceutically acceptable acid additionsalts with acids yielding pharmaceutically acceptable cations (e.g.hydrochloric or sulphuric acids).

The invention also includes pharmaceutical compositions comprising asactive ingredient a compound of the general formula (II) or apharmaceutically acceptable salt thereof in combination with apharmaceutically acceptable excipient and processes for producing suchcompositions which comprise admixing the active ingredient with theexcipient. Examples of excipients are starch, lactose, propylene glycol,triethanolamine, water and anti-fermentative agents.

According to a further aspect of the present invention there is provideda process for producing a compound of general formula (II) whichcomprises extracting tissue of a plant of the species Terminaliasericea, and in particular the roots or the bark of the roots with anorganic solvent, isolating sericic acid and/or sericoside from theextract and if desired converting the isolated sericic acid orsericoside to another compound of the general formula (II).

The organic solvent may, for example, be an alcohol (preferably a loweralcohol containing up to six carbon atoms and most preferably up to fourcarbon atoms, such as methanol, ethanol, n-propanol, isopropanol, or oneof the butanols), a ketone (preferably a di-lower alkyl ketone whereinthe lower alkyl groups contain up to six and preferably up to fourcarbon atoms as in acetone, methyl ethyl ketone and di-isopropyl ketone)or an ester (preferably an ester formed with a lower alcohol containingup to six carbon atoms, and most preferably up to four carbon atoms,such as methanol, ethanol, n-propanol, isopropanol, the butanols andamyl alcohol and a lower alkanoic acid containing up to four carbonatoms, such as formic, acetic, propionic or butyric acids).

Particularly useful solvents are ethanol, acetone and ethyl acetate.

Where the organic solvent is miscible with water, mixtures of thesolvent and water may be used.

Preferably, prior to isolating sericic acid and/or sericoside from theextract, fatty and resinous substances are removed, for example byevaporating the organic solvent from the extract and contacting theresidue so obtained with a liquid hydrocarbon so as to form a partiallypurified extract. Preferably, the residue is diluted with water or withan alcohol/water mixture before it is contacted with the hydrocarbon.The fatty and resinous substances are preferentially dissolved in thehydrocarbon and may therefore be removed by decanting the resultinghydrocarbon solution.

Sericic acid has been found to be generally more soluble in chlorinatedhydrocarbon solvents than in water and sericoside has been found to begenerally more soluble in aqueous solvents than chlorinatedhydrocarbons. The isolation of sericic acid and sericoside from thepartially purified extract obtained as described above thereforepreferably includes a fractionation step in which the extract isfractionated into a fraction containing sericic acid and othernon-glucosidated terpenes (Fraction A) and a fraction containingsericoside and other terpenic glucosides by contacting a solution of thepartially purified extract in water or a mixture of water and an alcohol(for example one of the alcohols specified above) with a chlorinatedhydrocarbon solvent such as, for example, chloroform, methylene chlorideor dichloroethane, and separating the aqueous and chlorinatedhydrocarbon solutions so obtained.

The aqueous solution may then be diluted with alcohol to give an alcoholconcentration of not less than 60% and treated to remove proteinaceousmaterial by adding neutral or basic lead acetate solution and filteringto remove any precipitate which is formed. The filtrate may then beevaporated to form an aqueous concentrate by eliminating the alcoholicsolvent and the terpenic glucosides extracted repeatedly from theconcentrate with a mixture of butanol and benzene (preferably 3:1 to4:1).

The solution in the butanol/benzene mixture may then be evaporated tosmall volume and the residue poured into isopropyl ether. Theprecipitate so obtained contains a major part of the terpenic glucosides(Fraction B).

Sericic acid and sericoside may be obtained from Fractions A and Brespectively by recrystallization or chromatographic separation.

It will be appreciated that the sericic acid- and sericoside-containingextracts of Terminalia sericea referred to above and in particular thepurified fractions referred to as Fractions A and B constitute furtheraspects of the present invention.

Sericic acid and sericoside may each be transformed into each of theother compounds of general formulae (II) by known methods ofesterification, hydrolysis, oxidation and salt formation and suchmethods form a further aspect of the present invention.

Thus, for example, sericic acid may be converted to sericoside byesterification with α-bromo-(tetra-acetyl)-glucose followed bysuccessive elimination of the acetyl radicals and sericoside may beconverted to sericic acid by saponification.

The following Examples illustrate the invention: EXAMPLE 1

A -- separation of Fractions A and B

200 kg. of finely ground roots of plants of the species Terminaliasericea are extracted under weak reflux four times using 600 liters ofaqueous alcohol each time. The reunited extracts are evaporated in vacuoto 100 liters and the aqueous residue extracted three times with ligroinusing 100 liters of ligroin each time. The ligroin, which contains fattyacids, resins and β-sitosterol removed from the residue is decanted andthe residue, in ethanol solution, is diluted with 300 liters of waterand extracted three times with dichloroethane using 100 liters eachtime.

The dichloroethane solution so obtained is evaporated to dryness invacuo and 2.5 kg. of residue are obtained containing sericic acid andother free triterpenes (Fraction A).

The aqueous residue remaining after the extraction with dichloroethaneis diluted with 500 liters of alcohol and 10 kg. of neutral lead acetatedissolved in 30 liters of alcohol are added. An abundant precipitate isformed and is left to stand overnight to sediment. The precipitate iscentrifuged and discarded, and the water-alcohol phase is concentratedin vacuo to about 200 liters. The aqueous concentrate is extracted threetimes with a mixture of t-butanol-benzene in the ratio 3:1 (v/v) using100 liters each time.

The organic phase is separated and washed with a 10% solution of sodiumcarbonate and then evaporated in vacuo to 20 liters. The butanolicconcentrate so obtained is poured, with vigorous agitation, into 150liters of diethyl ether. A precipitate comprising triterpenic glucosidesis formed and is centrifuged and dried. 5 kg. of product are obtained,containing sericoside and other triterpenic glucosides (Fraction B).

B -- preparation of purified sericic acid by crystallization

1 kg. of Fraction A is dissolved in 5 liters of alcohol. The solution isdecolorized with carbon, evaporated to 3 liters and left to standovernight.

300 g. of crude sericic acid crystallize, which by successiverecrystallisation from dilute aqueous alcohol or acetic acid enables 200g. of pure sericic acid having m.p. 278° -82° C., [α]_(D) ³⁰ =+ 37.8 (c=0.32 EtOH 95) to be obtained.

Additional quantities of sericic acid may be obtained by reuniting themother liquors, which are then evaporated to dryness, to obtain aresidue which is acetylated in acetone, using acetic anhydride. 80 g. ofsericic acid triacetate are obtained which after recrystallization fromglacial acetic acid melts at 183° C. and has [α]_(D) =+ 4° (c= 2, EtOH95) IR 3630 cm⁻¹ 1745 cm⁻¹ and 1705 cm⁻¹.

By saponification with alcoholic potash the sericic acid triacetate maybe converted to sericic acid, in a state of purity such that itsproperties are entirely identical with that obtained by crystallization,as described above.

C -- preparation of sericic acid by a chromatographic procedure

1 kg. of Fraction A is dissolved in 3 volumes of chloroform andchromatographed on a column containing 15 kg. of silica gel by elutingwith a solvent mixture comprising 95:5 chloroform-ethanol. The fractionscontaining the individual pure components are collected and reunited andafter crystallization from methanol, 250 g. of pure sericic acid havinga m.p. 278° - 82° C. are obtained along with 20 g. of arjunic acid withm.p. 220° - 22° C.

D -- preparation of sericoside by crystallization

1 kg. of Fraction B is dissolved in 6 liters of alcohol. The solution isdecolorized with carbon and evaporated to 3 liters. 1 liter of hot water(at about 50° C.) is added and the liquid is left to stand overnight.600 g. of crude sericoside crystallize which, after repeatedcrystallizations from dilute alcohol, furnish 250 g. of pure sericosidehaving the following characteristics: m.p. 206° -208° C. and [α]_(D) = +5.4 (c= 2, pyridine).

E -- preparation of sericoside by chromatography

1 kg. of fraction B is dissolved in 3 liters of an 8:2 (v/v)chloroform-ethanol mixture and chromatographed on 30 kg. of silica gelby eluting with the said solvent mixture. The fractions containing theindividual pure products are reunited and concentrated to dryness. Aftercrystallization from methanol there are obtained respectively 320 g. ofsericoside having an m.p. of 206° - 208° C. and 210 g. of arjunetine.

EXAMPLE 2

Preparation of methyl sericate

10 g. of sericic acid are dissolved in 50 ml. of chloroform and treatedwith a solution of diazomethane in methylene chloride until completereaction. The solution is concentrated in vacuo to dryness and theresidue is crystallized from acetone.

EXAMPLE 3

Preparation of tribenzoyl methyl sericate

10 g. of methyl sericate are dissolved in 50 ml. of anhydrous pyridineand 9.24 g. of benzoyl chloride are added. The reaction mixture is leftto stand for one night, then poured into water. Tribenzoyl methylsericate precipitates, and after crystallization from methanol has amelting point of 199° C.

EXAMPLE 4

Preparation of triacetyl 19-keto methyl sericate

10 g. of methyl triacetylsericate (prepared in an analogous manner tomethyl tribenzoyl sericate) are dissolved in 500 ml. of anhydrousacetone and Jones's reagent is added until the reaction is complete.

The acetone solution is diluted with 1,500 ml. of water whereupon theproduct precipitates in amorphous form.

The product is collected by filtration, and recrystallized from aqueousmethanol. After drying, there are obtained 9 g. of triacetyl 19-ketomethyl sericate having an m.p. of 200 and [α]_(D) = + 33 (c= 0.5, EtOH).

EXAMPLE 5

Preparation of diethylaminoethyl sericate

10 g. of potassium sericate are dissolved in 50 ml. of dimethylformamide and treated with 3 g. of diethylaminoethyl chloride. Thereaction mixture is kept at 50° C. for 5 hours, then poured into 600 ml.of water. An abundant precipitate forms which is filtered, washed withwater and recrystallized from aqueous isopropanol. The product melts at105° - 8° C. and [α]_(D) = +19.7° (c= 1, EtOH).

EXAMPLE 6

Preparation of methyl tetracetyl sericate

20 g. of methyl triacetylsericate are dissolved in 30 ml. of aceticanhydride and 1 ml. of concentrated perchloric acid is added. Thereaction mixture is left to stand for 1 hour, then poured into 500 ml.of water.

There is precipitation of the product which, after filtration, iscrystallized from ethanol.

The product melts at 223° C.

EXAMPLE 7

Preparation of methyl tetracetyl 18α-sericate

10 g. of methyl triacetyl sericate are dissolved in 50 ml. of 40%hydrobromic acid in acetic acid and left at room temperature for 30hours. The reaction mixture is poured into water. The product isfiltered and precipitates, and after drying it is crystallized fromhexane. 6 g. of methyl tetracetyl 18α-sericate are obtained having anm.p. of 194° C. and [α]_(D) =+12.6° (c= 0.4 in EtOH).

EXAMPLE 8

Preparation of 2,3,24-trihemisuccinyl derivative of sericic acid

10 g. of sericic acid are dissolved in 50 ml. of anhydrous pyridine and10 g of succinic anhydride are added.

The reaction mixture is reheated to 80° C. for 6 hours, then cooled anddiluted with 800 ml. of chloroform.

The solution is counter-washed with 10% aqueous HCl until the pyridineis eliminated and then concentrated to dryness and dehydrated over Na₂SO₄.

The residue is crystallized from glacial acetic acid and 11 g. oftrihemisuccinyl sericic acid with m.p. of 105° - 108° C. and [α]_(D)=+2.65° (c= 2, EtOH) is obtained.

By following the general procedures of the above Examples 2 to 8, butusing appropriate alternative reactants, other compounds of generalformulae (II) may be prepared.

The following pharmaceutical data is given to illustrate theanti-inflammatory and cicatrizing properties of the compounds of theinvention:

Anti-ulcer activity -- Gastric Ulcer in the rats induced by Shay'smethod

The anti-ulcer activity of sericic acid and sericoside was determined byadministering the compounds to rats in which gastric ulcers were inducedby Shay's method. The compounds were administered at the dose of 200mg./kg. orally five times, at 42, 30, 25 and 6 hours before tying of thepylorus and immediately after the operation and as shown in Table 1diminished the ulcer index by 48 and 45 percent respectively, comparedwith the controls.

                                      Table 1                                     __________________________________________________________________________                                             Percentage ulcer                     Treatment   Number of                                                                           Number of ulcers of each class (2)                                                               Ulcer                                                                             variation in rel-                                                                      Number of                                                                     non-ulcerated               Substance                                                                             mg/kg                                                                             animals                                                                             I   II  III IV  V  Index                                                                             ation to controls                                                                      stomachs (per               __________________________________________________________________________                                                      cent)                       Controls (gum     338 36  10  9   9  75  --       --                          arabic 10%)                                                                           --  13    (338)                                                                             (180)                                                                             (100)                                                                             (180)                                                                             (180)                                       Sericoside                                                                            200 13    369 15  1   0   3   39.5                                                                             -48      7.6                                           (369)                                                                             (75)                                                                              (10)                                                                              (0) (60)                                        Sericic acid                                                                          200 13    279 12  3   2   9  45  -45      --                                            (279)                                                                             (60)                                                                              (30)                                                                              (40)                                                                              (180)                                       __________________________________________________________________________     (1) Doses administered orally 5 times, 42, 30, 25 and 6 hours prior to an     immediately after the tying of the pylorus.                                   (2) In parentheses the product of the number of ulcers and the numerical      value attributed to the individual classes according to the individual        classes according to the evaluation criterion of T.O. Keyrilainen and M.K     Paasonen (Acta Pharmacol. et. Toxicol. 13, 22, 1957)                     

Ld 50 in Mice

The LD₅₀ in mice (as determined with intraperitoneal administration) forsericic acid and sericoside was as follows:

Sericic acid > 1,000 mg./kg.

Sericoside > 1,000 mg./kg.

Anti-inflammatory Activity Against Carragenin-induced Oedema in Rats

The anti-inflammatory activities of sericoside and sericic acid weredetermined by measuring the extent to which the oedema caused bysub-plantar administration of carragenin to rats could be inhibited byprior oral and intraperitoneal administration of the substances.

The following results were obtained:

    ______________________________________                                        1. Oral Administration                                                                        No.     Volume of oedema                                                                          Percentage                                        Doses   of      in ml. (Average ±                                                                      inhibition                                Treatment                                                                             mg/kg.sup.1                                                                           animals S.D).sup.2  of the oedema                             ______________________________________                                        Controls                                                                              --      10      0.30±0.005                                                                             --                                        Sericoside                                                                            200     10      *0.22±0.010                                                                            26                                        Sericic acid                                                                          200     10      *0.23±0.009                                                                            23                                        ______________________________________                                         *Significantly different (P < 0.05) from the average obtained with the        controls according to Student's "t" test.                                     .sup.1 Doses administered orally for 3 days; on the third day the             administration was effected two hours before the subplantar injection of      carragenin.                                                                   .sup.2 Maximum volume of the oedema measured 3 hours after the subplantar     injection of carragenin.                                                 

    ______________________________________                                        2. Intraperitoneal Administration                                                                     Volume of the                                                 Doses           oedema in ml.                                                                             Percentage                                        mg/kg   No. of  (Average ±S.D.)                                                                        inhibition of                             Treatment                                                                             (1)     animals (2)         the oedema                                ______________________________________                                        Controls                                                                              --      10      0.31±0.010                                                                             --                                        Sericoside                                                                            100     10      0.10±0.008 (*)                                                                         67                                        Sericic Acid                                                                          100     10      0.11±0.006 (*)                                                                         64                                        Controls                                                                              --      10      0.31±0.006                                                                             --                                        Sericoside                                                                             50     10      0.20±0.005 (*)                                                                         35                                        Sericic acid                                                                           50     10      0.23±0.008 (*)                                                                         25                                        ______________________________________                                         (*) Significantly different (P<0.05) from the average obtained with the       controls according to Student's "t" test.                                     (1) Administration endoperitoneally 30 minutes prior to the injection of      carragenin.                                                                   (2) Maximum volume measured after 3 hours.                               

Cicatrizing Activity Upon Experimental Wounds in Rats

The cicatrizing activity of sericic acid and sericoside uponexperimental wounds was determined on rats in accordance with the methodof Morton & Malone (Arch. Int. Pharmacodyn. Ther. 196, 117, 1972).

The treatment of the wounds was effected with a 10% suspension of theactive principles in water containing 2% carboxymethyl cellulose (CMC).The suspensions were used in doses of 0.1 ml. for each application, onetreatment being effected per day.

From the data shown in the following Table 2 it can be seen that sericicacid and sericoside possess significant healing activity, compared withthe controls, especially in the first days of treatment.

                                      Table 2                                     __________________________________________________________________________    Cicatrizing activity upon experimental wounds in the rat                                ml./rat/                                                                           Number of                                                                           Percentage remargination.                                                                       Average ± S.D.                      Treatment day  animals                                                                             Day I Day II                                                                              Day III                                                                             Day V Day VI                           __________________________________________________________________________    Control (2% CMC)                                                                        0.1  14    5.2±1.1                                                                          12.8±1.5                                                                         21.9±3.1                                                                         39.63±2.3                                                                        57.4±2.1                      Sericoside                                                                              0.1  14    13.9±1.4*                                                                        23.7±1.5*                                                                        36.8±2.0*                                                                        53.30±2.8*                                                                       68.2±2.1*                     Sericic acid                                                                            0.1  14    10.4±1.3*                                                                        23.7±2.3*                                                                        36.9±2.7*                                                                        48.00±1.5*                                                                       59.0±2.2                      __________________________________________________________________________     Note: Topical treatment effected on each of the days on which measurement     were taken (I, II, III, V, and VI).                                           (*)Significantly (P<0.05) different from the controls (2% CMC) based upon     Student's "t" test.                                                      

Activity Against Ultra-Violet Ray Erythema

Ultra-violet ray erythema in guinea pigs was effected in accordance withthe method of Winder et al. (Arch. Int. Pharmacodyn. 106, 261, 1968).

Sericoside and sericic acid were applied to the depilated skin of malealbino guinea pigs (average weight 300- 400 g) in the form of a 5% gel(using 200 mg. thereof) one hour prior to irradiation. The animals weredepilated 18 hours prior to the irradiation and irradiated for 3 minuteswith a 500 W. mercury vapor lamp at a distance of 18 cms.

The controls were treated with a similar gel which did not contain theactive ingredients, sericoside or sericic acid.

The compounds under examination were able to reduce the erythema with amost pronounced activity at 8 hours, as shown by the results set forthin the following Table 3.

                                      Table 3                                     __________________________________________________________________________    UV Erythema in the Guinea Pig                                                 Number of   Erythema Score**                                                  Treatment                                                                           animals                                                                             2 h.  4 h.  6 h.  8 h.  22 h.                                     __________________________________________________________________________    Controls                                                                            10    1.15±0.17                                                                        2.40±0.30                                                                        2.55±0.34                                                                        2.35±0.18                                                                        1.05±0.23                              Sericoside                                                                          10    0.75±0.17                                                                        1.70±0.23                                                                        1.95±0.22                                                                        1.30±0.25*                                                                       0.70±0.15                                          (34.8)                                                                              (29.2)                                                                              (23.5)                                                                              (44.7)                                                                              (33.3)                                    Sericic acid                                                                        10    0.95±0.12                                                                        1.80±0.21                                                                        2.05±0.22                                                                        1.35±0.18*                                                                       0.60±0.10                                          (17.4)                                                                              (25)  (19.6)                                                                              (42.5)                                                                              (42.8)                                    __________________________________________________________________________     * Significantly (P<0.05) different from the controls, according to            Duncan's test (analysis of the variation).                                    ** 0 = no erythema; 0.5 = moderate reddening; 1 = marked reddening; 2 =       obvious erythema.                                                             Note: The percentage inhibition compared with the controls is entered in      parentheses.                                                             

Pharmaceutical Preparations

The following examples of pharmaceutical preparations were prepared byadmixing the active ingredients with the excipients referred to andillustrate the manner in which the compounds of the invention may bebrought into forms suitable for topical and oral administration.

    ______________________________________                                        1 % Gel for Topical Application                                               1) Sericoside           1         g.                                           Excipients (propylene glycol,                                                 Carbopol 934, ethyl                                                           alcohol, triethanolamine, water,                                                                     100       g.                                           antifermentative) q.s.                                                       2) Sericic acid         1         g.                                           Excipients (propylene glycol,                                                 Carbopol 934, ethyl                                                           alcohol, triethanolamine, water,                                                                     100       g.                                           antifermentative) q.s.                                                       1 % Ointment for Topical Application                                          Sericoside              1         g.                                          Excipients (glycerine, cetyl alcohol,                                         saturated vegetable                                                           triglycerides, lanoline oil, propylene                                                                100       g.                                          glycol, water) q.s.                                                           Suspension for Oral Administration                                            Sericic acid            1         g.                                          Excipients (sodium alginate, corn starch,                                     saccarose,                                                                    water, antifermentative) q.s.                                                                         100       g.                                          Powder for Topical Application                                                1) Sericoside           2         g.                                           Excipients (Microlan, corn starch,                                            magnesium stearate,                                                           talc) q.s.             100       g.                                          2) Sericic acid         2         g.                                           Excipients (Microlan, corn starch,                                            magnesium                                                                     stearate, talc) q.s.   100       g.                                          Ampoule for Injection                                                         1) Sericic acid         10        mg.                                          Excipients (propylene glycol,                                                 ethyl alcohol, sterile                                                        pyrogen free water) q.s.                                                                             1         ml.                                         2) Sericoside           20        mg.                                          Excipients (propylene glycol,                                                 ethyl alcohol, sterile                                                        pyrogen-free water) q.s.                                                                             2         ml.                                         Confections                                                                   1) Sericoside           20        mg.                                          Excipients (corn starch, lactose,                                             talc, magnesium                                                               stearate, sodium alginate, sugar,                                             gum arabic,                                                                   magnesium carbonate) q.s.                                                                            250       mg.                                         2) Sericic acid         10        mg.                                          Excipients (corn starch, lactose,                                             talc, magnesium                                                               stearate, sodium alginate, sugar,                                             gum arabic,                                                                   magnesium carbonate) q.s.                                                                            200       mg.                                         Transparent gel                                                               Sericic acid            10        g.                                          Excipients (propylene glycol,                                                 triethanolamine, water,                                                       antifermentative) q.s. to                                                                             200       g.                                          Transparent gel                                                               Sericoside              5         g.                                          Excipients (propylene glycol,                                                 triethanolamine, water,                                                       antifermentative) q.s. to                                                                             200       g.                                          Tablets                                                                       Sericoside              100       mg.                                         Excipients (starch, lactose) q.s. to                                                                  500       mg.                                         ______________________________________                                    

I claim:
 1. Sericoside, having the general formula ##STR4## in pureform.
 2. Sericoside in accordance with claim 1 in crystalline form.
 3. Amethod of eliciting an anti-inflammatory effect in an animal, whichcomprises administering, topically, orally or by injection, ananti-inflammatory amount of sericoside.
 4. A method of eliciting ananti-inflammatory effect in an animal, which comprises administering,topically, orally or by injection, an anti-inflammatory amount of acompound as defined in claim
 1. 5. A pharmaceutical compositionconsisting essentially of an anti-inflammatory amount of sericoside, anda pharmaceutically acceptable excipient.
 6. A method of eliciting acicatrizing effect in an animal, which comprises administering,topically, orally or by injection, a cicatrizing amount of sericoside.7. A method of eliciting a cicatrizing effect in an animal, whichcomprises administering, topically, orally or by injection, acicatrizing amount of a compound as defined in claim
 1. 8. Apharmaceutical composition consisting essentially of a cicatrizingamount of sericoside, and a pharmaceutically acceptable excipient.
 9. Amethod of eliciting an anti-inflammatory effect in an animal, whichcomprises administering, topically, orally or by injection, ananti-inflammatory amount of a composition in accordance with claim 5.10. A method of eliciting a cicatrizing effect in an animal, whichcomprises administering, topically, orally or by injection, acicatrizing amount of a composition in accordance with claim 8.